Three Steps to Prepare for Difficult Family Encounters
Drash (Teaching) on Parshat VaYishlach
Zvika Krieger, Chochmat HaLev
Delivered on December 1, 2023

Many of us just returned from spending time with family over Thanksgiving. How was that for you? Some of us are planning on heading home for the holidays, whether Chanukah, Christmas, Winter Break. How are you feeling about that?

This can be a challenging time of year for a lot of us. We spend much of our lives differentiating from our families of origin, building our own identities, designing a life that aligns with values of who we are today. And then a few times a year, we’re thrust back into where it all began, with the people who remind us of who we used to be, where we’ve come from – and in many cases, who we’ve been trying to get away from.

These reunions can be particularly challenging during times of strife in the world. How many of you had difficult Thanksgiving conversations with your families about Israel-Palestine? At the Thanksgiving dinner I went to, our gracious host set a “No Israel-Palestine” rule. Are you dreading that conversation over the holidays this month? Are you dreading conversations about Israel-Palestine with anyone in your life – friends, neighbors, co-workers?

Part of what is so challenging about these conversations is that they create distance between us and our loved ones – and perhaps highlight the distance we’ve traveled from them. I pride myself on being a pretty calm and grounded person. When I get in those situations, I suddenly morph into an argumentative, defensive, short-fused, unempathetic person that I hardly recognize. 

As often happens, this week’s Torah portion has some wisdom to offer. Our ancestor Yaakov (Jacob) is preparing for an uncomfortable homecoming of his own. After tricking his father into giving him the blessing meant for his brother Esav (Esau), he flees in fear of Esav’s retribution. After 20 years away, four wives and 13 children later, his father on his deathbed, Yaakov finally decides it’s time to go home. And you thought your Thanksgiving table was awkward?

Yaakov knows it’s not going to be easy. He assumes Esav is still angry at him, and may even want to kill him. So he prepares his servants for this difficult encounter by saying that, before they go, they must be ready to answer three questions from Esav: 


Who are you for?

אָ֣נָה תֵלֵ֔ךְ

Where are you going?

לְמִ֖י אֵ֥לֶּה לְפָנֶֽיךָ

Who is in front of you?

Rabbi Levi Yitzchak of Berditchev, the early Hassidic mystic, teaches that in preparing his servant, Yaakov was actually preparing himself. These three questions are an ancestral blueprint that we can use to prepare to navigate challenging relationships in our lives. And perhaps, like Yaakov and Esav, answering these questions for ourselves can help us achieve some level of resolution and healing with our loved ones. 

The first question to ask yourself is  לְמִי־אַ֙תָּה֙ – Who are you for?

When you’re in relationship with someone who sees the world differently, it’s important to get clear on who you are: what are your values, who are you in service of, what do you stand for. That doesn’t mean that you shouldn’t be open to learning new things, having your perspective challenged, broadening your horizons. But in order to be available for that, you need to feel confident in your own sense of self. You need to know that someone criticizing your opinion doesnt mean you are a bad person or there is something wrong with you.

This can be particularly challenging with family or old friends, who may have an outdated notion of who you are or their own expectations of who they still want you to be. If you feel good about who you are – and who you’ve become – then it is a lot easier to engage with people who have made different choices about their lives, especially those who have no qualms sharing their judgements about the choices you’ve made.  

Some of you know that I have been speaking out for nuance and complexity in regards to the Israeli-Palestinian conflict, reassuring us that we have the capacity to care about multiple struggles and sufferings at the same time. Many of you have reached out to share how much you appreciate this message; thank you for that. But not everyone agrees. 

Someone who I know from growing up in the Orthodox world, who now lives in Israel and who I haven’t spoken to for almost two decades, read one of my recent sermons and reached out to me with a heated response. I’ll spare you the most vitriolic parts of her message, but here is how she ended: “Shame on you for presenting their sides when your family is here fighting for their lives. This is not a game. You forgot who you are. But don’t worry, they won’t!”

I’m used to getting critical messages from people who disagree with me, but I had to spend some time contemplating why this one stung particularly hard. Maybe it was the line, “You forgot who you are.” It felt like I was being accused of abandoning an older, better version of myself. I contemplated what I’ve given up in becoming the person who I am today – what blindspots I may have developed, what values I may have compromised. 

But then I realized what she meant: “You’ve forgotten who you were. You are no longer like me, and the people who you used to be in community with.” She’s right. I have moved on from those older versions of myself. And I like who I am today. I can have empathy for the people who remain in that world, who remain those older versions of themselves, if I can stay connected with what I love about the person who I have become. לְמִי־אַ֙תָּה֙ – Who are you for?

The second question to ask yourself is אָ֣נָה תֵלֵ֔ךְ – Where are you going?

This feels like a particularly poignant question to ask ourselves when we go home for the holidays: Why am I here? Why did I come back? Why did I choose to put myself in a situation that will inevitably be uncomfortable and triggering? Maybe part of it is inertia – that’s just what we do during the holidays. Maybe it’s good-old Jewish guilt – “We haven’t seen you in months, when are you coming home?”

But there’s something deeper. Perhaps you’re looking for connection. Maybe you want a sip of that love that can only come from the family that raised you or from the people who have known you the longest. Maybe you just want to be taken care of. Maybe you want to get away from your crazy adrenaline-packed routine and reconnect to a simpler time in your life. 

Take a moment to reflect on a complicated relationship in your life – why do you stay in it? With all the drama, the stress – what makes it worth it? What do you really want? If you can stay connected to that golden nugget, it will make it easier to weather the turbulence that distracts you from that desire. אָ֣נָה תֵלֵ֔ךְ – Where are you going?

The first question to ask yourself is לְמִ֖י אֵ֥לֶּה לְפָנֶֽיךָ – Who is in front of you?

In context of this week’s Torah portion, this question is referring to all the livestock and cattle that Yaakov’s family brings with them. Applied to our own lives, I see this as an invitation to remind ourselves, when heading into these tense situations: who and what am I bringing with me? I don’t have to do this alone. What allies do I have available to me? Are there people who I can literally bring with me to help buoy me during these tense interactions? Or are there people who can be available for a supportive text or phone call when things get rough? 

What about frameworks for difficult conversations, like non-violent communication, that I could use? Or short prayers or verses that I can easily call up to  help ground me? Yaakov reminds us: Don’t go into these situations empty-handed. Don’t just wing it. Come prepared. 

לְמִ֖י אֵ֥לֶּה לְפָנֶֽיךָ – Who is in front of you? We can also read this as an invitation to be present in the moment. So often in challenging situations, we get caught in our heads, spinning stories and judgements that become increasingly disconnected from what is happening right in front of us. When you catch that happening, take a breath. What is happening Lefanecha – right here, right now. What am I feeling in my body? How is my heart-rate? Am I feeling tired? Hungry? What is the person across from me actually saying, as separate from the narrative we may be making up about their words? What is the most charitable way I can choose to interpret their words or actions? 

And who is the person that is actually in front of me, rather than someone else they are reminding me of? What old patterns might I be projecting on others, rather than reacting to them as they are today? What old stories might be we re-enacting, rather than allowing ourselves and our loved ones to write new stories? 

לְמִ֖י אֵ֥לֶּה לְפָנֶֽיךָ – come prepared with both external and internal resources to support you in this important work of relational healing. 

So as you head into difficult conversations over the next few weeks – whether traveling to see our families, or even with folks right here at home, try to block off some time to ask yourself these three questions as a way to set yourself up for success:


Who are you for?

אָ֣נָה תֵלֵ֔ךְ

Where are you going?

לְמִ֖י אֵ֥לֶּה לְפָנֶֽיךָ

Who is in front of you?

Notice which ones of these questions resonate the most with you, and which ones might be difficult to answer. Notice which ones make you defensive and which help you feel grounded. Notice how you might interpret these questions differently as you prepare to heal a challenging relationship in your own life. 

I’ve been thinking about that second question: אָ֣נָה תֵלֵ֔ךְ – Where are you going? Perhaps it can serve a reminder that we’re all on a journey. When I acknowledge that I am a work-in-progress, it’s easier for me to weather criticism. There’s nothing better to take the sting out of a barb than by responding: You’re right. I’m not perfect. I do make mistakes. Just because I’m not perfect and just because I make mistakes does not make me a bad person.

So my blessing to all of us, at this time of tension on both the personal and global level, is that we hold ourselves with compassion. אָ֣נָה תֵלֵ֔ךְ – you’re walking the path, you’re doing your best. 

And by holding ourselves with compassion, may we be able to marshall compassion for others, and bring about peace in ourselves, in our relationships, and between the descendants of Yaakov and Esav across the globe. 

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